Many have asked publicly and privately for my side of
"The Date", so here goes..
"The Date", so here goes..
When Deb first asked me about a fantasy date, I admit that I was both intrigued and skeptical at the same time, having limited experience in such things and having been out of the meat market scene for some time, I felt a bit unprepared to "date" again.
I have always been somewhat of a shy person at heart, and meeting women in bars has not been my forte, however, I love pleasing DD and so I dredged up my acting lessons of the past and decided to throw myself into the project with abandon.
One of DD's conditions before the date was that we would have limited physical contact with each other the week leading up to the date, thus imposing on me a limitation of touching and kissing as I'm apt to do. No bedtime kiss, no goodbye kiss in the morning and most certainly no nipple tweaking at any time. I love tweaking DD's nipples as it really turns her on, and I mean literally. She has said before that they're connected directly to her pussy, and I enjoy seeing the expression on her face and gasps from her mouth as I slowly pinch those hard nipples.
The day of the date was one of those that start and continue with difficulty; you know the ones - you spill your coffee on your best shirt, stub your toe, and generally lose all sense of timing for any and all projects you're involved with. This was one of those days.
I was almost late for the date due in part to these foibles, and left the house in a rush, knowing that DD would have arrived at the bar earlier than me, and getting a bit nervous, what being in a new place and all.
Driving was a bitch as it was raining pretty good, and of course there was a lack of street parking and I'd be damned if I was going to pay for valet service. That's just the way I am: lavish gifts and goodies on my friends, but not on myself most of the time.
Driving around the block twice, I then noticed a sweet space right across the street from the old hotel / condo where the bar was located, and snagged it post haste. My luck runs this way most of the time - I'm just one of those people that many hate because I snag the good spots - I can't explain it, it's just a gift.
Exiting the elevator to the darkened bar on the 13th floor, I checked myself in the mirror for any imperfections. Normal for me, not vanity, just being a professional. "Damn I look good" came to mind.
Snaking through the bar looking for DD I saw a light assortment of other professionals, and although the bar was bathed in darkness, it had a comfy feel to it. Not seeing DD, I noticed that there was more seating on the other side of the bar, and so turning the corner, was surprised to see DD sitting at on one of the stools smack in the center of the bar. This threw me for a second, but I regained my composure and asked her "Is this seat taken?" in the most suave and charming voice I could muster.
"No" she replied coolly, so I seated myself and waited for the bartender to notice me.
Glancing over at DD out of the corner of my eye, I was thrilled to see that she was dressed much more professionally than when she left the condo earlier in the morning, and had had her hair done in almost a suicidegirls/emo/goth look with a red choker surrounding her neck. MEOW! I almost creamed my pants as I glanced at her.
Her tone when she spoke was cool and professional, and I attempted to engage her in conversation by politely asking her if she minded if I smoked while I drank.
"I suppose not".
Filthy habit I know, but I was more than a bit nervous at that point.
I made some comment about it being a lousy hard day at work and attempted to draw her out with more small talk.
"So, what do you do for a living?" I asked.
"I'm a sex therapist, but don't tell me about your dreams, OK?" she answered, and I almost choked on my gin as she said it.
The small talk went on for some time, and I was trying to remain aloof as DD talked to the bartenders about how they were from or had been to the same small towns, and I downed my double Sapphire and motioned for more.
After some more small talk laced with innuendos about work et-cetera, and the second gin working on me by this point, I made some comment about food and asked DD if she had eaten yet.
"No" came the answer, so I asked her if she would join me for a bite (to eat, I made clear) downstairs at the restaurant. "No strings" I said.
DD said yes, so we paid our bar tabs, gathered our coats, and took off towards the elevator.
That was probably one of the strangest one minute elevator trips I've ever been on, with an uncomfortable silence filling the small mirrored car as we traveled downwards.
I must admit that dinner was quite good, but I could tell that DD was a bit uncomfortable there, surrounded by 20 somethings as we were, and so instead of coffee and desert at the end of dinner, I told her that I had a most excellent gourmet coffee at my house, and would she care for some and a nightcap.
Agreeing, we left the restaurant and talked about what kind of car she was driving, where I was parked in relation to her, and how we would get back to my place. I asked her if she would like an escort to the garage, and she answered affirmatively as the underground parking was a bit dark.
I offered her my cell phone number, and told her to call me when she exited the garage so she wouldn't get lost, and left her for my own car parked at the front of the building.
The drive back to the condo was speedy to say the least, as I found myself behind a police car in the far left lane doing well over the speed limit, and as I myself love to drive fast, followed him at a discrete distance with DD not far (I hoped) behind.
I had asked DD if she knew where our exit was off the highway, so I knew if she fell too far behind, I would slow down once I reached it in order for her to catch up.
Pulling into the condo complex and exiting my car, I motioned for her to park across from me, and then escorted her into the house.
Taking her furry coat from her and putting it away, she intoned that she thought that I had a pretty nice place.
"Nice fireplace too" she said, and so I walked over to it and leaning on the mantle looked at her and said "You think so? Watch this!" as I flipped the electrical switch on the side of the wall that ignited the gas flame.
"Just give me a couple of minutes for the coffee" I told her as I reached for the pot.
"Would you like some Bailey's Irish Cream in it as well?" I enquired.
"Certainly", DD replied as she made herself comfortable on the living room futon.
I brought the liquored coffee over to DD and set down beside her, both of us savoring the warmth and smell of the rich brew with the extra kick of alcohol in it.
Chatting for a while, she finished her coffee and set it on the coffee table, and when she turned back to me, she looked a bit woozy from the Bailey's, and so I invited her to stay the night since it was getting late and the weather was bad, mentioning that I had a spare room that she could sleep in.
"All alone?" she asked.
"Well, my cat Penny can keep you company" I replied coyly.
“So it’s up to Penny who I sleep with tonight?”
A bit of small talk ensued, but then I turned to her and deepened my voice and intoned softly but firmly I commanded "Take off your blouse."
The look on her face was one of shock and excitement, and she did what I asked.
As I looked at her sitting there for a moment, I then asked her to take off her bra.
I almost caught a look of "What kind of girl do you think I am?" on her face, laced like her bra with an air of excited sexual tension.
DD took off her bra and let it drop to the floor and I reached over to caress her milky white mounds, and slightly twist those hard nipples that I had missed over the last week.
Moaning softly, I pulled myself closer and kissed her passionately, our tongues entwining around each other.
"Pull my cock out" I said softly as I leaned into her ear, and she willingly did as I again commanded, eagerly loosening my belt and pants.
By this time my cock was standing at full attention, harder than I remember it for some time, and I remember just wanting to fuck the shit out of DD right then and there, but the acting came first as I told her to lose the rest of her clothing.
Stepping out of her pants, I saw that she had chosen to wear a favorite pair of her Boy Shorts panties, ones that I loved seeing her wear, along with black stockings and a garter. These things I saw then: a gorgeously sexy creature with large natural breasts, a choker, and beautiful lace panties, and I had no choice but to next command her to suck my throbbing member.
Long slow slurps quickly turned into eager sucking as my shaft moved quicker and quicker into her mouth, my powerful thrusts almost choking her at one point.
When I could stand it no longer, I led DD into my bedroom, turned the light dimmer on to the lowest setting, and pushed her gently down on the bed, her legs spread open for me to see a glimmer of moistness past her boy shorts.
My friends, by this time my cock was raging hard and I couldn't stand it any more, so I mounted DD and thrust my cock into her with gentle force, fucking her with passion that I had not known for quite some time.
We fucked like mad people for quite some time until I upended her legs and took her panties off to be presented with a quite smooth shaved pussy, beaded with pussy juice and begging to be licked.
Excusing myself for a moment, I hurried out to get the camera, knowing that this was turning into a world-class fuck, and wanting to capture it all on film and video if at all possible. Returning quickly, I dove into DD's muff and licked her with abandon, sliding my fingers in and out at the same time until she cried out in passion like never before.
Begging me to stop as she was getting over-stimulated, I pulled her up so she could suck on my cock again. Slurping and slobbering over my dick like the champ she is, I attempted to take pictures of her as she gave me a world class blow job.
I wish all the male readers of this blog could experience the deftness that DD brings to oral sex, I really do.
Being able to stand it no more, I told DD to get on her knees, and entered her pussy from behind, thrusting and shoving like a wild animal that I had become, before she came all over my cock, drenching it in sweet DD juices.
My god, we went at it for quite a while before we fell over on our backs, and DD begged me to "End Scene", to which I readily agreed.
Now, my feelings about the whole date.
I really attempted to go back to my acting training throughout the whole scene and play it as if I had never met the girl before. This can be hard at times, because let's face it - you know the person.
You must detach yourself from the whole situation and really FEEL like you've never seen this other person before, not just go through the motions as it were.
When I walked into the bar, I was going for an after work drink. Really, that's how I felt.
I just happened to see a woman that looked soooo sexy, and with a bit of kink, that I knew I had to hit on her.
Truthfully, there was a point at the bar when our small talk was going poorly that I had to turn to my experiences in sales to get where I needed to be, which was sticking my dick into this luscious creature and fucking the hell out of her like so many of had done when we were "on the prowl".
A good salesman never takes no for an answer, and queries his prey (sales is very akin to hunting after all) as to their objections in order to overcome them.
Back to how it all came together.
You must remain in character and resist the urge to say or do something that you would do normally around your partner.
Look at it this way: remember when you're at work or a social situation and you meet new people. You don't automatically assume that they know everything about you, nor do you LET them know everything about you until your relationship has progressed further. The same is true in fantasy role playing.
The more "real" you can make and feel through the situation, the better time you will have in the end. Remember, you are both trying to recreate the excitement that you both felt the first time you met, or to put it more succinctly, how it felt when you were back on the Great Hunt.
So I played it to the hilt, catching myself when I would do or say anything that would be "out of character" for me if I was really out on a date.
This whole experience has widened me in a way that I really enjoyed, and I hope to do something of this nature again with DD.